109996-70-5

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 63096-02-6 N-tert-butoxycarbonyl-L-leucine methyl ester 
• 108-98-5 thiophenol 
• 109996-54-5 (2R,3S)-3-<(tert-butyloxycarbonyl)amino>-1-(phenylthio)-2-hydroxy-5-methylhexane 
• 107202-51-7 (2R)-2-[(1S)-1-[N-(tert-butyloxycarbonyl)amino]-3-methylbutyl]oxirane 

Downstream Products

• 109996-38-5 ((S)-1-{(S)-1-[(S)-1-((R)-2-Benzenesulfonyl-1-hydroxy-ethyl)-3-methyl-butylcarbamoyl]-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of chiral, enantiopure allylic amines by the Julia olefination of α-amino esters

The four-step conversion of a series of N-Boc-protected L-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes.